Chiral (OC)Ru(salen)-catalyzed tandem sulfimidation and [2,3]sigmatropic rearrangement: asymmetric CN bond formation

✍ Scribed by Masakazu Murakami; Tsutomu Katsuki

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 67 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)00603-2

✦ Synopsis

Asymmetric C N bond formation was achieved in a highly enantioselective manner by using (OC)Ru(salen)-catalyzed sulfimidation and the subsequent [2,3]sigmatropic rearrangement: treatment of allyl aryl sulfides with p-toluenesulfonyl azide in the presence of a catalytic amount of (OC)Ru(salen) followed by hydrolysis of the resulting N-allyl-N-arylthio toluenesulfonamides provided N-allyl toluenesulfonamides of high enantiomeric excess.